Dichloromethane → HCID 118566708, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2,6-dichloro-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide (150 mg, 0.37 mmol, 1.00 eq) in 1,4-Dioxane (4.00 mL, 26.67 V) and water (0.50 mL, 3.33 V) was degassed with nitrogen for 15 minutes, then to this 1-methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (101.25 mg, 0.44 mmol, 1.20 eq), cesium carbonate (362.17 mg, 1.10 mmol, 3.00 eq) and [1,1-bis(diphenyl phosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (30.15 mg, 0.04 mmol, 0.10 eq) were added, then the reaction mixture was heated in pressure tube at 100° C. for 5 h. After completion of the reaction by TLC, the reaction mixture was cooled to room temperature, and filtered through celite, washed with ethyl acetate, and the filtrate was concentrated under reduced pressure to provide the crude compound, which was purified by column chromatography to afford the title compound (90 mg, 0.17 mmol, 47.5%) as a dark brown solid. m/z: 434.2 [M+H]+

Provenance & Evidence